Signs your boss is a human:

  • She breathes.
  • He eats lunch.
  • She uses words like “weekend.”
  • He comes in some mornings and says, “I’m tired.”
  • She leaves on Thursday and is all, “Thank the lord tomorrow is Friday.”
  • He sometimes gets a little bit of his lunch on his keyboard, and wipes it up with his shirt when he thinks no one is looking.

You get what I’m saying: Bosses are human beings, too. Sure, they make more money than you. And sure, they have the fancier title—but they’re not infallible, and they do make mistakes. I certainly hope not life-changing ones, but definitely double-booking-on-the-schedule level errors.

Take me for example: I’m a boss. And I occasionally mess up—in the office, and in the Chipotle line when I’m being rushed. (May she who said “no guac” when she meant “guac, yes, obviously guac” cast the first stone.)

Back in my underling days of yore, I used to spend hours stressing out about whether or not I should tell my manager that he made a mistake. I would sit in my chair, wringing my hands in agony, weighing out the pros and cons of saying something. Then, by the time I did, he’d respond, “Why didn’t you tell me this morning?” and I’d have to say, “Um, because I didn’t want to hurt your feelings?”

After getting promoted to a managerial role and seeing the situation from the other side, I realized none of that stress was ever worth it. One of my writers at a former company used to approach me using the same tone of voice usually reserved for tragic deaths:

“Excuse me, Jenni, Ms. Maier, Madame, um, I think, OK, there might be a typo, or it might totally be on purpose, in that article you just put up. But, you know, I’m also bad at reading, so I’m probably just dumb.”

Nine-and-a-half times out of 10, there was a typo in the article. And I was always happy when it was brought to my attention. Not only did I want a typo-free site for my brand’s sake, but I also wanted it for my reputation’s sake. After all, I am an ed-i-tor (pronounced in that fancy French way that demands you dangle a long cigarette out of your mouth).

While there are certainly supervisors out there who take this very personally (and if that’s the case, know that it will be more out of embarrassment than anger toward you, even if the reaction seems otherwise), odds are high that your boss will be happy you helped him or her look better. Assuming, of course, that you do it the right way.


How to Do It

I promise you that it’s much less complicated than you’re making it out to be—just approach the situation politely and directly.

I say politely to remind you that people usually aren’t proud of their mistakes, so having a tone that even remotely reeks of “you stupid over-paid chump, here I am again, doing your job for you” won’t help it go over well. Especially since this (hopefully) isn’t about one-upping your manager and making her feel stupid.

And I say directly, because your boss is busy. There’s no time to beat around the bush. Yes, he or she has feelings (as pointed out above), but he or she also just wants to know what’s up. So, there’s no need for a long email laying out every possible, hypothetical reason it’s not a mistake.

Just go for something simple like this:

Hi Boss,

I saw that you scheduled our marketing meeting for 2 PM today, however I have my dentist appointment then. Can we reschedule? I’m available that morning before noon and Wednesday between 3 to 5 PM. 

Let me know if either of those times work for you,

Dutiful Employee

Or this:

Hi Manager,

I just received your email about the accounting error. I’m guessing you meant to send that to someone else, so I wanted to let you know. Don’t worry—I’ll keep it confidential.

Professional Subordinate

Done.

Now see, that’s a lot easier than spending your morning Googling, “How do I hack into an email account to unsend something?” Especially because your boss will most likely respond with some variation of, “Whoops, you’re right.” And life will go on as normal.


Photo of co-workers talking courtesy of Shutterstock.